The study of new variations of the Claisen Rearrangement and the Ireland ester enolate rearrangement is proposed. Such processes could well find ready application to new stereospecific annelation strategies. In particular, we hope to address this new methodology to a stereospecific synthesis of the hypolipidemic agent, compactin as well as to new syntheses of quinolines and indoles of potential pharmaceutical interest including ergot species. A new approach to stereospecific heterofunctialization is proposed. Such methodology might find application in the synthesis of carbohydrates.